Prostate cancer remains a leading cause of cancer-related mortality in men, particularly when the disease progresses to aggressive, therapy-resistant stages. Small-molecule drug discovery benefits from the rapid synthesis and comparison of structurally related compounds to identify molecules with improved potency and selectivity. Phenoxathiin-10,10-dioxide derivatives represent a promising chemical scaffold that can be explored through systematic structural modification. However, current synthetic approaches require multiple isolated steps and repeated purifications, resulting in significant loss of time and material. This project aims to redesign the synthetic route to phenoxathiin-10,10-dioxide derivatives by developing a more efficient one-pot strategy. In this approach, key reaction steps will be performed sequentially in a single vessel using Lewis acid or base catalysis, eliminating the need to isolate intermediates. Reaction conditions will be optimized through systematic screening of catalyst combinations, temperature, and solvent systems. Reaction progress will be monitored using thin-layer chromatography, and products will be confirmed by NMR spectroscopy. The anticipated outcome is a streamlined synthetic workflow that reduces reaction time and material loss relative to the existing multi-step procedure. In addition, a focused library of approximately ten phenoxathiin-10,10-dioxide analogs will be generated to support future biological evaluation and assess their potential relevance for prostate cancer therapeutic research.